First asymmetric total synthesis of penarolide sulfate A(1)
| Title | First asymmetric total synthesis of penarolide sulfate A(1) |
| Publication Type | Journal Article |
| Year of Publication | 2008 |
| Authors | Mohapatra, DK, Bhattasali, D, Gujar, MK, Khan, MIslam, Shashidhara, KS |
| Journal | European Journal of Organic Chemistry |
| Issue | 36 |
| Pagination | 6213-6224 |
| Date Published | DEC |
| Type of Article | Article |
| ISSN | 1434-193X |
| Keywords | Asymmetric synthesis, C-C coupling, Dihydroxylation, epoxidation, Macrocycles, Regioselectivity, Total synthesis |
| Abstract | Penarolide sulfate A(1), with three contiguous stereogenic centers on a macrocyclic skeleton, affords promise as an alpha-glucosidase inhibitor. Herein, we describe the first asymmetric total synthesis of this natural product. A stereoselective strategy for rapid assembly of the complete framework of the 30-membered macrocyclic core is delineated herein. Sequential amidation and intramolecular Sonogashira cross-coupling reactions were pivotal to the success of our efforts. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) |
| DOI | 10.1002/ejoc.200800680 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.068 |
Divison category:
Biochemical Sciences
Organic Chemistry